CA1193272A - Betalactames - Google Patents

Betalactames

Info

Publication number: CA1193272A
Authority: CA; Canada
Prior art keywords: formula; beta; lactam; compound; amino
Prior art date: 1980-10-31
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000461837A

Other languages

English (en)

Inventor

Eric M. Gordon

Miguel A. Ondetti

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

ER Squibb and Sons LLC

Original Assignee

ER Squibb and Sons LLC

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1980-10-31

Filing date

1984-08-24

Publication date

1985-09-10

1980-10-31 Priority claimed from US06/202,830 external-priority patent/US4337197A/en

1984-08-24 Application filed by ER Squibb and Sons LLC filed Critical ER Squibb and Sons LLC

1985-09-10 Application granted granted Critical

1985-09-10 Publication of CA1193272A publication Critical patent/CA1193272A/fr

Status Expired legal-status Critical Current

Links

-1 beta-lactam hydroxamic acids Chemical class 0.000 title claims description 71
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 21
239000001257 hydrogen Substances 0.000 claims abstract description 20
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
125000000217 alkyl group Chemical group 0.000 claims abstract description 15
YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 claims abstract description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
238000002360 preparation method Methods 0.000 claims abstract description 6
150000001875 compounds Chemical class 0.000 claims description 61
238000000034 method Methods 0.000 claims description 43
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 40
125000006239 protecting group Chemical group 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 10
150000002431 hydrogen Chemical class 0.000 claims description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 claims description 5
239000003960 organic solvent Substances 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 5
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 4
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 claims description 4
229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
238000010992 reflux Methods 0.000 claims description 4
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 3
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
238000010438 heat treatment Methods 0.000 claims 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 2
WLHCBQAPPJAULW-UHFFFAOYSA-N 4-methylbenzenethiol Chemical compound CC1=CC=C(S)C=C1 WLHCBQAPPJAULW-UHFFFAOYSA-N 0.000 claims 1
125000005948 methanesulfonyloxy group Chemical group 0.000 claims 1
239000000543 intermediate Substances 0.000 abstract description 4
230000000844 anti-bacterial effect Effects 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 49
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 43
239000000243 solution Substances 0.000 description 37
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 27
229910001868 water Inorganic materials 0.000 description 27
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 26
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 23
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
239000011541 reaction mixture Substances 0.000 description 18
239000000203 mixture Substances 0.000 description 17
239000007787 solid Substances 0.000 description 17
239000000047 product Substances 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 15
150000003839 salts Chemical class 0.000 description 14
125000002252 acyl group Chemical group 0.000 description 13
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 12
230000008018 melting Effects 0.000 description 12
238000002844 melting Methods 0.000 description 12
229910052757 nitrogen Inorganic materials 0.000 description 12
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 11
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 11
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 10
125000004432 carbon atom Chemical group C* 0.000 description 10
229910052938 sodium sulfate Inorganic materials 0.000 description 10
235000011152 sodium sulphate Nutrition 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 9
239000000284 extract Substances 0.000 description 9
229910052736 halogen Inorganic materials 0.000 description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
229940073584 methylene chloride Drugs 0.000 description 9
150000002367 halogens Chemical class 0.000 description 8
238000003756 stirring Methods 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
239000002253 acid Substances 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
150000002500 ions Chemical class 0.000 description 6
150000003951 lactams Chemical class 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 6
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 5
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
239000004473 Threonine Substances 0.000 description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 5
239000002808 molecular sieve Substances 0.000 description 5
239000011347 resin Substances 0.000 description 5
229920005989 resin Polymers 0.000 description 5
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 5
125000000446 sulfanediyl group Chemical group *S* 0.000 description 5
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 5
229960002898 threonine Drugs 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 4
125000004429 atom Chemical group 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
125000000753 cycloalkyl group Chemical group 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
239000006260 foam Substances 0.000 description 4
238000004108 freeze drying Methods 0.000 description 4
239000000463 material Substances 0.000 description 4
229910052700 potassium Inorganic materials 0.000 description 4
239000011591 potassium Substances 0.000 description 4
239000000843 powder Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
FBPINGSGHKXIQA-UHFFFAOYSA-N 2-amino-3-(2-carboxyethylsulfanyl)propanoic acid Chemical compound OC(=O)C(N)CSCCC(O)=O FBPINGSGHKXIQA-UHFFFAOYSA-N 0.000 description 3
LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 3
JTNCEQNHURODLX-UHFFFAOYSA-N 2-phenylethanimidamide Chemical compound NC(=N)CC1=CC=CC=C1 JTNCEQNHURODLX-UHFFFAOYSA-N 0.000 description 3
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 3
229930182555 Penicillin Natural products 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
125000004442 acylamino group Chemical group 0.000 description 3
238000005917 acylation reaction Methods 0.000 description 3
125000003342 alkenyl group Chemical group 0.000 description 3
125000004414 alkyl thio group Chemical group 0.000 description 3
125000003368 amide group Chemical group 0.000 description 3
239000000538 analytical sample Substances 0.000 description 3
239000002585 base Substances 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
125000004093 cyano group Chemical group *C#N 0.000 description 3
238000010511 deprotection reaction Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000001914 filtration Methods 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 3
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 3
239000010410 layer Substances 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
150000002960 penicillins Chemical class 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
229910000343 potassium bisulfate Inorganic materials 0.000 description 3
150000003222 pyridines Chemical class 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
125000000547 substituted alkyl group Chemical group 0.000 description 3
DRTQHJPVMGBUCF-UCVXFZOQSA-N 1-[(2s,3s,4s,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical class O[C@H]1[C@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UCVXFZOQSA-N 0.000 description 2
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 2
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
LXUNZSDDXMPKLP-UHFFFAOYSA-N 2-Methylbenzenethiol Chemical compound CC1=CC=CC=C1S LXUNZSDDXMPKLP-UHFFFAOYSA-N 0.000 description 2
GTSKMJQRWNTAJH-UHFFFAOYSA-N 2-methoxyimino-2-(1,3-thiazol-4-yl)acetic acid Chemical compound CON=C(C(O)=O)C1=CSC=N1 GTSKMJQRWNTAJH-UHFFFAOYSA-N 0.000 description 2
JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
241000124008 Mammalia Species 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
230000010933 acylation Effects 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
229940024606 amino acid Drugs 0.000 description 2
150000001413 amino acids Chemical class 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000012267 brine Substances 0.000 description 2
125000002837 carbocyclic group Chemical group 0.000 description 2
150000001718 carbodiimides Chemical class 0.000 description 2
125000002091 cationic group Chemical group 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000013078 crystal Substances 0.000 description 2
125000000392 cycloalkenyl group Chemical group 0.000 description 2
238000010828 elution Methods 0.000 description 2
150000002148 esters Chemical group 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
125000001072 heteroaryl group Chemical group 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
238000007327 hydrogenolysis reaction Methods 0.000 description 2
SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
229940111688 monobasic potassium phosphate Drugs 0.000 description 2
235000019796 monopotassium phosphate Nutrition 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
HYDZPXNVHXJHBG-UHFFFAOYSA-N o-benzylhydroxylamine;hydron;chloride Chemical compound Cl.NOCC1=CC=CC=C1 HYDZPXNVHXJHBG-UHFFFAOYSA-N 0.000 description 2
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 2
239000002243 precursor Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910052979 sodium sulfide Inorganic materials 0.000 description 2
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
239000000126 substance Substances 0.000 description 2
230000019635 sulfation Effects 0.000 description 2
238000005670 sulfation reaction Methods 0.000 description 2
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
239000000725 suspension Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
125000003396 thiol group Chemical group [H]S* 0.000 description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
NTNKNFHIAFDCSJ-UHFFFAOYSA-N (2-nitrophenyl) thiohypochlorite Chemical compound [O-][N+](=O)C1=CC=CC=C1SCl NTNKNFHIAFDCSJ-UHFFFAOYSA-N 0.000 description 1
UUPQXPOQKUEZPC-UHFFFAOYSA-N (2-oxoazetidin-1-yl) hydrogen sulfate Chemical compound OS(=O)(=O)ON1CCC1=O UUPQXPOQKUEZPC-UHFFFAOYSA-N 0.000 description 1
MGOGKPMIZGEGOZ-REOHCLBHSA-N (2s)-2-amino-3-hydroxypropanamide Chemical compound OC[C@H](N)C(N)=O MGOGKPMIZGEGOZ-REOHCLBHSA-N 0.000 description 1
FNHVSHKKUKMXJJ-VIFPVBQESA-N (2s)-3-hydroxy-2-[(2-phenylacetyl)amino]propanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)CC1=CC=CC=C1 FNHVSHKKUKMXJJ-VIFPVBQESA-N 0.000 description 1
PZUOEYPTQJILHP-GBXIJSLDSA-N (2s,3r)-2-amino-3-hydroxybutanamide Chemical compound C[C@@H](O)[C@H](N)C(N)=O PZUOEYPTQJILHP-GBXIJSLDSA-N 0.000 description 1
ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
IQVADDJLQDIUIC-UHFFFAOYSA-N 2,6-dimethylpyridine;sulfur trioxide Chemical compound O=S(=O)=O.CC1=CC=CC(C)=N1 IQVADDJLQDIUIC-UHFFFAOYSA-N 0.000 description 1
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 1
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241000283690 Bos taurus Species 0.000 description 1
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102000001324 CD59 Antigens Human genes 0.000 description 1
108010055167 CD59 Antigens Proteins 0.000 description 1
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241000283086 Equidae Species 0.000 description 1
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FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
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241001024304 Mino Species 0.000 description 1
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239000005708 Sodium hypochlorite Substances 0.000 description 1
241001455617 Sula Species 0.000 description 1
AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 1
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TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical class C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
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150000007513 acids Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
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150000001342 alkaline earth metals Chemical class 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
125000004457 alkyl amino carbonyl group Chemical group 0.000 description 1
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125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
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IAJRTXSNYRHBSI-UHFFFAOYSA-N azetidin-1-yl hydrogen sulfate Chemical compound OS(=O)(=O)ON1CCC1 IAJRTXSNYRHBSI-UHFFFAOYSA-N 0.000 description 1
HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 1
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QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
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239000003782 beta lactam antibiotic agent Substances 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
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GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000000872 buffer Substances 0.000 description 1
GUGRBFQNXVKOGR-UHFFFAOYSA-N butyl hypochlorite Chemical compound CCCCOCl GUGRBFQNXVKOGR-UHFFFAOYSA-N 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
LXWBXEWUSAABOA-VXSYNFHWSA-N cephamycin C Chemical compound S1CC(COC(N)=O)=C(C(O)=O)N2C(=O)[C@@](OC)(NC(=O)CCC[C@@H](N)C(O)=O)[C@H]21 LXWBXEWUSAABOA-VXSYNFHWSA-N 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000007822 coupling agent Substances 0.000 description 1
125000004966 cyanoalkyl group Chemical group 0.000 description 1
UVJHQYIOXKWHFD-UHFFFAOYSA-N cyclohexa-1,4-diene Chemical compound C1C=CCC=C1 UVJHQYIOXKWHFD-UHFFFAOYSA-N 0.000 description 1
125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 1
229960003077 cycloserine Drugs 0.000 description 1
XBPCUCUWBYBCDP-UHFFFAOYSA-O dicyclohexylazanium Chemical compound C1CCCCC1[NH2+]C1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-O 0.000 description 1
125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
239000012154 double-distilled water Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
239000007789 gas Substances 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
150000002390 heteroarenes Chemical class 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
230000036571 hydration Effects 0.000 description 1
238000006703 hydration reaction Methods 0.000 description 1
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
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238000011065 in-situ storage Methods 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical compound [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
HDDIWWOSKAMMMH-VIFPVBQESA-N n-[(3s)-1-hydroxy-2-oxoazetidin-3-yl]-2-phenylacetamide Chemical compound O=C1N(O)C[C@@H]1NC(=O)CC1=CC=CC=C1 HDDIWWOSKAMMMH-VIFPVBQESA-N 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
125000006501 nitrophenyl group Chemical group 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229940056360 penicillin g Drugs 0.000 description 1
KAVGMUDTWQVPDF-UHFFFAOYSA-N perflubutane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)F KAVGMUDTWQVPDF-UHFFFAOYSA-N 0.000 description 1
229950003332 perflubutane Drugs 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical class [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
LVTHXRLARFLXNR-UHFFFAOYSA-M potassium;1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [K+].[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F LVTHXRLARFLXNR-UHFFFAOYSA-M 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
239000012521 purified sample Substances 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000012048 reactive intermediate Substances 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
239000000523 sample Substances 0.000 description 1
238000006748 scratching Methods 0.000 description 1
230000002393 scratching effect Effects 0.000 description 1
229960001153 serine Drugs 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
241000894007 species Species 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
238000004448 titration Methods 0.000 description 1
JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
208000019206 urinary tract infection Diseases 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1

Classifications

- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA000461837A 1980-10-31 1984-08-24 Betalactames Expired CA1193272A (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US202,830		1980-10-31
US06/202,830 US4337197A (en)	1980-10-31	1980-10-31	O-sulfated β-lactam hydroxamic acids and intermediates
CA000388104A CA1179339A (fr)	1980-10-31	1981-10-16	ACIDES .beta. -LACTAM HYDROXAMIQUES O-SULFATES

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000388104A Division CA1179339A (fr)	1980-10-31	1981-10-16	ACIDES .beta. -LACTAM HYDROXAMIQUES O-SULFATES

Publications (1)

Publication Number	Publication Date
CA1193272A true CA1193272A (fr)	1985-09-10

Family

ID=25669462

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000461837A Expired CA1193272A (fr)	1980-10-31	1984-08-24	Betalactames

Country Status (1)

Country	Link
CA (1)	CA1193272A (fr)

1984
- 1984-08-24 CA CA000461837A patent/CA1193272A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2002-09-10	MKEX	Expiry
2023-05-26	MKEX	Expiry	Effective date: 20020910

Publication	Publication Date	Title
EP0051381B1 (fr)	1985-01-30	Acides bêta-lactame hydroxamiques 0-sulfatés
US4576749A (en)	1986-03-18	3-Acylamino-1-carboxymethylaminocarbonyl-2-azetidinones
CA1246572A (fr)	1988-12-13	2-oxo-1-[[(sulfonyl substitue)amino]- carbonyl]azetidines
EP0076758B1 (fr)	1987-01-07	Dérivés 4-éther d'acides 2-azétidinone-1-sulfoniques
EP0085291B1 (fr)	1988-08-17	2-Oxo-1-(aminocarbonylaminosulfonylaminocarbonyl)-azétidines
US4533660A (en)	1985-08-06	Antibacterial O-sulfated β-lactam hydroxamic acids
EP0068466B1 (fr)	1987-01-14	Sels (aryl ou hétéroaryl) thio-4 oxo-2 azétidine-sulfoniques-1 et leur procédé de préparation
US4499016A (en)	1985-02-12	2-Oxo-1-[(acylamino)sulfonyl]azetidines
CA1253502A (fr)	1989-05-02	Sels de l'acide 4-[[(amidomethyl)oxy]methyl]- 2-oxo-1-azetidinesulfonique
US4734496A (en)	1988-03-29	4-amino derivatives of 2-oxo-1-azetidinesulfonic acid salts
EP0061763B1 (fr)	1986-06-18	Sels de l'acide 4-mercapto-substitué-2-oxo-1-azétidine sulphonique et procédé de préparation
FR2581062A1 (fr)	1986-10-31	Acides b-lactame hydroxamiques o-sulfates, a action therapeutique
US4548751A (en)	1985-10-22	(2-Oxo-1-azetidinyloxy)-2-propenoic acid
NZ205642A (en)	1986-08-08	Beta-lactams and pharmaceutical compositions
EP0124123B1 (fr)	1989-04-19	3-Acylamine-1-sulphonylaminocarbonylméthoxy-2-azétidinones
GB2103212A (en)	1983-02-16	4-Substituted derivatives of 2-oxo-1-azatidinesulfonic acid salts
CA1254218A (fr)	1989-05-16	Acide 3-(3-acylamino-2-oxo-1-azetidinyl)-4-oxo-2- butenoique
US4889930A (en)	1989-12-26	Process for making 2-oxo-1-((substituted sulfonyl)amino)carbonzyl)azetidines and intermediates used therein
CA1243679A (fr)	1988-10-25	3-ACYLAMINO-2-OXO-1-AZETIDINYL-.beta.-OXYPROPIONATES
JPS5978199A (ja)	1984-05-04	ホスホン酸、リン酸およびリン酸エステルの３−アシルアミノ−２−オキソ−１−アゼチジニルエステル類
CA1272726A (fr)	1990-08-14	2-oxo-1-(aminocarbonylaminosulfonyl-aminocarbonyl) azetidines
JPS6094958A (ja)	1985-05-28	アゼチジノン類
EP0135814A1 (fr)	1985-04-03	1-(1H-tétrazol-5-yl-alcoxy)-2-azétidinones
DE3122795A1 (de)	1982-12-30	"monocyclische (beta)-lactam-antibiotika"